1, 5 pentanediol bis-cyclohexyl acetate



Patented Mar. 7, 1950 UNITED STATES PTENT OFFICE 1,5 PENTANEDIOL BIS-CYCLOHEXYL ACETATE Stanford J. Hetzel, Cheltenham, Pa., assignor to Sun Oil Company, Philadelphia, Pa., a corpora-- tion of New Jersey No Drawing. Application August 25, 1948, Serial No. 46,182

1 Claim. (01. 260-468) 2 The present invention relates to a novel com- Grams pound derived from 1,5-pentanediol Cut #2-210 C.-216 C./4 mm. Hg.

H H H H H (product of the invention) 109.6 g g g, g g Cut 3above 216 o./4 mm. Hg. (poly- I l I 5 meric material-residue) H H H H H specifically to 1,5-pentanediol bis-cyclohexyl- The product of this invention is a colorless to acetate amber oil-like material having a boiling point at H2 H2 O l rm m-oHd Lo-omom.cmomom-o-o-no CH: H\ CH: HaO /(')H: o o H: H7

and to its method of preparation. 5 mm. Hg. of about 210 C.-216 C., a refractive According to the invention the foregoing ester index of 1,5-pentanediol was prepared by refluxing in 0 the presence of a trace of para-toluene sulfonic N D 1-4726 acid approximately stoichiometric quantities of 20 1,5-pentanediol and cyclohexylacetic acid in presence of a solvent, for example commercially available xylenes. 20C. To suppress the formation of partial ester an 4 excess of the cyclohexylacetic acid should be employed The ester of this invention has been found useother acid catalysts can be employed For ful as a plasticizer for polyvinyl resins such as example sulfuric acid, hydrochloric acid and Polyvinyl chloride and polyvinyl Chloride-Polyother acids commonly used in esterification Vmyl acetate mixturesprocesses can be employed in minor quantities. n copending DD n for Patent S a No- Other Solvents for example t m or even 46,187, filed by the instant inventor August 25,

and a density of higher boiling aromatics can be employed s 1- 1948, there is described and claimed a polyvinyl vents inert under the conditions of the reaction resin in p i d mp siti n with the est r also can be used, of this invention.

The following is an example of the preparation I 01mm: of t ester of t i i t 1,5-pentaned1o1bis-cyclohexylacetate.

STANFORD J. I-IETZEL. Example 120 grams cyclohexylacetic acid (0.78 mole) REFERENCES CITED Was heated und r refluxing conditions w 3 The following references are of record in the grams (0.37 mole) of 1,5-pentanediol and 250 cc. file of this patent:

xylene for 8 hours. Two grams of para-toluene sulfonic acid was used as a catalyst. Water from UNITED STATES PATENTS the esterification was removed continuously in a DeanStark tube. The reaction product was Number Name Date washed with 20% aqueous solution of sodium g i et a1 f-g, carbonate and dried over anhydrous calcium 2017070 g i er 2: 935 chloride. Xylene was removed and the remainder 2208'960 g -gg- 1940 of the reaction mass was distilled taking three 5 2339387 Endres 1944 cuts as follows: i

. Grams OTHER REFERENCES Cut #1-bo1ling below 210 C./4 mm. Hg.

(unreacted 1,5-pentanediol and half- ,Ser. No. 367,292, Berg et al. (A. P. C.), pubester) 9.5 lished April 20, 1943. 

